EP0652799A1 - Terminal-group-closed anti-foaming agents. - Google Patents
Terminal-group-closed anti-foaming agents.Info
- Publication number
- EP0652799A1 EP0652799A1 EP93915971A EP93915971A EP0652799A1 EP 0652799 A1 EP0652799 A1 EP 0652799A1 EP 93915971 A EP93915971 A EP 93915971A EP 93915971 A EP93915971 A EP 93915971A EP 0652799 A1 EP0652799 A1 EP 0652799A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- carbon atoms
- foaming agents
- acid
- carboxylic acids
- polyglycol ethers
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D19/00—Degasification of liquids
- B01D19/02—Foam dispersion or prevention
- B01D19/04—Foam dispersion or prevention by addition of chemical substances
- B01D19/0404—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
- C07C69/24—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with monohydroxylic compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/47—Levelling agents
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/74—Carboxylates or sulfonates esters of polyoxyalkylene glycols
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0026—Low foaming or foam regulating compositions
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2093—Esters; Carbonates
Definitions
- the invention relates to new end group-capped antifoams which are obtained by completely or partially esterifying fatty alcohol polyglycol ethers with carboxylic acids and to the use of these agents as defoamers in a large number of applications.
- Another field in which anti-foaming agents are used is the wastewater treatment of sewage treatment plants.
- air is blown into the wastewater, for example, which ensures intimate mixing and the meeting of the dirt particles with the microorganisms [ChiuZ 25, 87 (1991)].
- the resulting foam is protein foam in many cases and therefore particularly resistant. Instead of sedimentation, there is an undesired fixing of the solids in and on the foam lamellae, which makes it difficult to separate the sewage sludge.
- fatty alcohol polyglycol ethers which have been end-capped have proven their worth in recent years. These so-called “mixed ethers” are obtained in the sense of Williason's ether synthesis by reacting fatty alcohol polyglycol ethers with alkyl halides [DE-Cl-37 44 525, Handle].
- esters of fatty alcohols with di- and polycarbonic acids are also known which act as defoamers. For many applications, however, these products are not sufficiently water-soluble.
- the object of the invention was therefore to provide new anti-foaming agents, the production of which is free from the disadvantages described.
- the invention relates to new end-capped anti-foaming agents which are obtained by adding fatty alcohol polyglycol ethers of the formula (I)
- R 1 for an aliphatic, linear or branched hydrocarbon radical having 1 to 22 carbon atoms and 0, 1 1, 2 or 3 double bonds
- R- for hydrogen or a Methyl group and n stands for numbers from 1 to 40, esterified with carboxylic acids in the presence of acidic catalysts.
- esters have a good foam-suppressing action and are sufficiently stable even in an alkaline environment over the usual periods of use. Compared to the mixed topic of the prior art, their production is not associated with the inevitable occurrence of salts. They are also characterized by their particularly easy biodegradability and low fish toxicity.
- the invention further relates to a process for the preparation of end-capped anti-foaming agents, in which fatty alcohol polyglycol ethers of the formula (I)
- R 1 is an aliphatic, linear or branched hydrocarbon radical having 1 to 22 carbon atoms and 0, 1, 2 or 3 double bonds
- R - is hydrogen or a methyl group
- n is a number from 1 to 40
- Fatty alcohol polyglycol ethers which are considered as starting materials for the production of the new anti-foaming agents in the sense of the invention, are known substances which are produced industrially by addition of ethylene and / or propylene oxide onto primary alcohols. Depending on the ture of the catalyst used, the products can have a conventional or preferably a narrowed homogeneous distribution.
- Typical examples are addition products of 1 to 40, preferably 2 to 10, mol of ethylene and / or propylene oxide onto capron alcohol, caprylic alcohol, capric alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidylyl alcohol, linolenic alcohol , Arachyl alcohol, gadoleyl alcohol, behenyl alcohol and erucyl alcohol and their technical mixtures, such as are obtained, for example, in the hydrogenation of technical fatty acid methyl ester fractions or aldehydes from Roelen's oxosynthesis.
- Fatty alcohol polyglycol ethers of the formula (I) are preferably used, in which R 1 represents alkyl radicals having 2 to 18, in particular 8 to 18, carbon atoms, R2 represents hydrogen and n represents numbers from 2 to 10.
- the fatty alcohol polyglycol ethers mentioned can be esterified by aliphatic or aromatic, optionally hydroxyl-substituted carboxylic acids having 6 to 22 carbon atoms.
- aliphatic carboxylic acids are caproic acid, caprylic acid, isononanoic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, linoleic acid, linolenic acid, ricinoleic acid, 12-hydroxyachearic acid Gadoleic acid, behenic acid and erucic acid and their technical mixtures which can be obtained, for example, by pressure splitting of Greases and oils.
- aromatic carboxylic acids are benzoic acid and the isomeric phthalic acids. Saturated aliphatic carboxylic acids having 8 to 18 carbon atom
- the esterification of the polyglycol ethers with the carboxylic acids can be carried out in a manner known per se.
- suitable acidic catalysts are mineral acids, sulfonic acids or acidic ion exchangers. Typical examples are sulfuric acid, methanesulfonic acid, p-toluenesulfonic acid or surfactant sulfonic acids; Tin grinding has also proven itself as a catalyst for the esterification of aromatic carboxylic acids. It is advisable to use the catalysts in amounts of 0.5 to 5% by weight, based on the carboxylic acids.
- the esterification reaction can be carried out at temperatures from 80 to 120, preferably 90 to 110 ° C. In order to shift the reaction equilibrium to the side of the products, it is advisable to remove the condensation water continuously. If desired, the acid catalyst can be neutralized after the esterification.
- the new antifoam agents are notable for their foam-suppressing action and good ecotoxicological compatibility.
- Another object of the invention therefore relates to the use of the end group-sealed anti-foaming agents according to the invention for foam regulation in detergents, dishwashing detergents and cleaners, lacquers and paints, as auxiliaries for the sugar and yeast industry and in the wastewater treatment of sewage treatment plants.
- the formulation was as foam promoter to 6 wt .-% of an adduct of average 12 mol of ethylene oxide to a Ci2 / L4 Ko ° k s i n f ettam added to 0.25.
- the mixture was injected through a nozzle into a measuring vessel at a temperature of 31 ° C., pumped around continuously, and the foam height obtained was read off from the liquid phase.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Dispersion Chemistry (AREA)
- Toxicology (AREA)
- Materials Engineering (AREA)
- Emergency Medicine (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Hydrogenated Pyridines (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4225236 | 1992-07-30 | ||
DE4225236A DE4225236A1 (en) | 1992-07-30 | 1992-07-30 | End-capped antifoams |
PCT/EP1993/001938 WO1994003251A1 (en) | 1992-07-30 | 1993-07-21 | Terminal-group-closed anti-foaming agents |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0652799A1 true EP0652799A1 (en) | 1995-05-17 |
EP0652799B1 EP0652799B1 (en) | 1996-11-20 |
Family
ID=6464486
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP93915971A Revoked EP0652799B1 (en) | 1992-07-30 | 1993-07-21 | Terminal-group-closed anti-foaming agents |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0652799B1 (en) |
JP (1) | JPH07509180A (en) |
AT (1) | ATE145346T1 (en) |
DE (2) | DE4225236A1 (en) |
ES (1) | ES2093975T3 (en) |
WO (1) | WO1994003251A1 (en) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19518476A1 (en) * | 1995-05-19 | 1996-11-21 | Basf Ag | Pivalic acid esters of alkoxylated aliphatic alcohols |
DE19802733B4 (en) * | 1998-01-26 | 2006-08-24 | Cognis Deutschland Gmbh & Co. Kg | Anti-foaming agents |
DE19940797A1 (en) | 1999-08-27 | 2001-03-01 | Goldschmidt Ag Th | Obtained by Akoxylierung block copolymers, styrene oxide-containing polyalkylene oxides and their use |
DE102005011608A1 (en) | 2005-03-14 | 2006-09-21 | Basf Ag | Esterified alkyl alkoxylates as low-foaming surfactants |
WO2009027456A2 (en) | 2007-08-29 | 2009-03-05 | Basf Se | Esterified alkyl alkoxylates as solid low-foam wetting agents |
WO2010108858A1 (en) * | 2009-03-26 | 2010-09-30 | Dr. W. Kolb Ag | Component for deaerating a process water especially during paper production |
WO2019023016A1 (en) * | 2017-07-28 | 2019-01-31 | Croda, Inc. | Cleaning formulation comprising a solvent additive |
CN118043304A (en) | 2021-10-01 | 2024-05-14 | 科莱恩国际有限公司 | End-capped bio-based low foaming surfactants |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3800492A1 (en) * | 1988-01-11 | 1989-07-20 | Henkel Kgaa | FOAM CONTROL AGENT FOR THE PRODUCTION AND PROCESSING OF FOODSTUFFS OR FOR FERMENTATION PROCESSES |
IL95029A0 (en) * | 1989-07-12 | 1991-06-10 | Gaf Chemicals Corp | Low viscosity defoaming/antifoaming formulations |
DE4041754A1 (en) * | 1990-12-24 | 1992-06-25 | Henkel Kgaa | USE OF SPECIAL CARBONIC ESTERS AS A FOAM CONTROL |
-
1992
- 1992-07-30 DE DE4225236A patent/DE4225236A1/en not_active Withdrawn
-
1993
- 1993-07-21 AT AT93915971T patent/ATE145346T1/en not_active IP Right Cessation
- 1993-07-21 ES ES93915971T patent/ES2093975T3/en not_active Expired - Lifetime
- 1993-07-21 DE DE59304555T patent/DE59304555D1/en not_active Revoked
- 1993-07-21 WO PCT/EP1993/001938 patent/WO1994003251A1/en not_active Application Discontinuation
- 1993-07-21 JP JP6504789A patent/JPH07509180A/en active Pending
- 1993-07-21 EP EP93915971A patent/EP0652799B1/en not_active Revoked
Non-Patent Citations (1)
Title |
---|
See references of WO9403251A1 * |
Also Published As
Publication number | Publication date |
---|---|
WO1994003251A1 (en) | 1994-02-17 |
JPH07509180A (en) | 1995-10-12 |
DE4225236A1 (en) | 1994-02-03 |
EP0652799B1 (en) | 1996-11-20 |
DE59304555D1 (en) | 1997-01-02 |
ES2093975T3 (en) | 1997-01-01 |
ATE145346T1 (en) | 1996-12-15 |
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